| 100% | SAYSOMETHING | 12 | Song for which A Great Big World and Christina Aguilera won the Grammy for Best Pop Duo/Group Performance in 2015: 2 wds. |
| 60% | OLDTOWNROAD | 11 | Song for which Lil Nas X and Billy Ray Cyrus won the Grammy for Best Pop Duo/Group Performance in 2020: 3 wds. |
| 51% | STRESSEDOUT | 11 | Song for which Twenty One Pilots won the Grammy for Best Pop Duo/Group Performance in 2017: 2 wds. |
| 42% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 40% | VISIONOF | 8 | "___ Love," song by Mariah Carey for which she won the Grammy for Best Female Pop Vocal Performance: 2 wds. |
| 39% | TOWN | 4 | "Old ___ Road," song by Lil Nas X featuring Billy Ray Cyrus that won the Grammy Award for Best Pop Duo/Group Performance in 2020 |
| 39% | MORE | 4 | "Kiss Me ___," song by Doja Cat ft. SZA that won the Grammy Award for the Best Pop Duo/Group Performance in 2022 |
| 37% | YOU | 3 | "Someone like ___," hit song by Adele that won the Grammy for Best Pop Solo Performance in 2012 |
| 37% | SAY | 3 | "___ Something," 2013 Grammy-winning duet by A Great Big World and Christina Aguilera |
| 37% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 36% | STARTED | 7 | "Let's Get It ___," 2004 song by the Black Eyed Peas that won a Grammy for Best Rap Performance by a Duo or Group |
| 36% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 36% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 36% | COUNTRYFOROLD | 13 | "No ___ Men," a movie in which Javier Bardem starred in and won the Best Actor Award at the Oscars for his performance: 3 wds. |
| 36% | IWANTED | 7 | "Everything ___," song by Billie Eilish which won the Grammy for Record of the Year in 2021: 2 wds. |
| 35% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 35% | JENNIFERHUDSON | 14 | Singer who won the Oscar for Best Performance in a Supporting Role for "Dreamgirls": 2 wds. |
| 35% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 35% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 35% | TRUTH | 5 | "___ Hurts," song by Lizzo which won the 2020 Grammy for Best Pop Solo Performance |
| 35% | THISISME | 8 | Song from "The Greatest Showman" which won the Golden Globe Award for Best Original Song in 2017: 3 wds. |
| 34% | SUPERWOMAN | 10 | Song from 17a which won Alicia Keys a Grammy for Best Female R&B Vocal Performance in 2009 |
| 34% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 34% | MYFAITHINYOU | 12 | "If I Ever Lose ___," single that won Sting a Grammy Award for Best Pop Vocal Performance (Male) in 1994: 4 wds. |
| 34% | AWHOLE | 6 | "___ New World," song from "Aladdin" that won the Academy Award for Best Original Song in 1993: 2 wds. |
| 34% | KATHYGRIFFIN | 12 | "My Life on the D-List" star who won a Grammy for Best Comedy Album in 2014: 2 wds. |
| 34% | INCHNAILS | 9 | Nine ___, band whose song "Wish" won the 1993 Grammy for Best Metal Performance: 2 wds. |
| 34% | HARRY | 5 | ___ Styles, "Watermelon Sugar" singer who won the Grammy for Best Pop Solo Performance in 2021 |
| 34% | TANEHISICOATES | 14 | "Between the World and Me" author who won a "genius grant" in 2015: 2 wds. |
| 33% | STEVEMARTIN | 11 | "L.A. Story" actor whose "The Crow: New Songs for the 5-String Banjo" won the Best Bluegrass Album Grammy in 2010: 2 wds. |